


Nobody Does It Like You Do

by waitingforjudas



Series: Judas' Kinktober 2019 [4]
Category: Supernatural
Genre: Castiel is Loved (Supernatural), Cunnilingus, Daddy Kink, Dean Winchester Has a Daddy Kink, Dean is a woman, F/M, Fisting, Gags, Genderswap, Kinktober, Kinktober 2019, Vaginal Fisting, and Dean, because of magic, by me, we stan cas
Language: English
Status: Completed
Published: 2019-10-04
Updated: 2019-10-04
Packaged: 2020-11-22 05:28:18
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,120
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20868932
Author URL: https://archiveofourown.org/users/waitingforjudas/pseuds/waitingforjudas
Summary: Dean’s sick of this curse—he just wants to have sex with his boyfriend again! But Dean’s insecure on the best of days, and at the moment, he’s got a lot to be insecure about.But when Cas opens his eyes to the bright side of temporary womanhood, Dean decides to make the best of a strange situation.Written for Kinktober 2019 prompts: Gags, Cunnilingus, Daddy, and Fisting.





	Nobody Does It Like You Do

**Author's Note:**

> I have never questioned my gender, and I’ve never written genderswap. I am not a trans person and I completely identify with the sex I was assigned at birth. 
> 
> I’m also telling the story through the perspective of a man who, in my headcanon, was abused, shamed for anything “girly” or “gay,” and therefore has a lot of internalized problems with accepting himself for who he is, especially when that deviates from the societal norm. 
> 
> Therefore, **if I have written something offensive in this story, I am _always_ ready to listen and change things.** The last thing I want to do is write something that hurts somebody. This goes for all of my stories, too. 
> 
> Title is from “Daddy Issues” by The Neighbourhood. 
> 
>   
_Written for Kinktober 2019. Prompt list can be found at https://twitter.com/NihilistShiro/status/1162794889970511872._

Dean hated this. He _hated_ this, with a fiery, burning, raging passion. 

He had to _sit down to pee_. 

No, but really, the worst part wasn’t that he had to worry about his hair—because according to Sam’s research, there was a chance that if he cut his hair in this form, his own hair was going to be cut proportionally (if he gave himself a bob, he’d get a buzz cut). 

It wasn’t even that he had to get an entirely new fucking wardrobe, including an ill-fitting sports bra that felt like it crushed his lungs and threatened to snap his ribs (that he refused to wear unless he was leaving the house, and then only because creepy men would hit on him if he didn’t). 

The _worst_ part was that it had been a week and he just wanted to have sex with his gorgeous boyfriend. 

It wasn’t even for lack of trying on Cas’ part—it was just that every time Dean thought about the possibility of having sex with him, he got a little bit… tense. 

The most recent time that Cas had given him more than the most chaste peck possible—three hours ago, and Dean _was_ counting—Dean had spent twelve minutes cursing him out and snapping half-baked excuses and explanations for why they shouldn’t have sex. 

Sam had walked in halfway through, blinked, and turned around and left before Dean could change topics and snap at him for poking his nose into business that clearly wasn’t his. 

Now, Dean was moping in his bed, blasting music in his headphones and trying to forget the fact that he didn’t have a penis anymore. Or seven inches of his height. Or eighty pounds of _pure muscle_… and cheeseburgers. 

Something tapped his shoulder and his eyes flew open, hand going to the angel blade at his side and pinning whoever it was in a matter of seconds. 

Oh—_oh shit_. It was just—

“Cas,” Dean said weakly, not taking off his headphones just yet as he let Cas up. He couldn’t stand the sound of his own damn voice—high and soft and _not his_. 

Cas offered him a somewhat-crushed bouquet of sunflowers and mimed taking off headphones. 

Dean reluctantly did so, leaving the flowers in his lap. “What?”

“I’m sorry I made you uncomfortable,” Cas said, shifting on the mattress. “I really didn’t intend to. I don’t know what I did that’s made you so uncomfortable touching me, but I hope that you can let me know or give me enough time to understand it. And in the meantime, I won’t pressure you, okay? Are platonic touches okay?” 

It all came out in one fast rush, like releasing a floodgate. 

“Did you prepare that?” Dean asked instead. 

Castiel nodded, dropping his gaze. “Yes. Would you prefer I avoid touching you at all?”

Dean huffed, staring at the sunflowers because Cas was just—just too hard to look at then. 

“That’s fine,” Cas said, standing, and Dean looked up, frowning. “I’m grateful for the clarif—”

“What?”

“You— You wanted— I won’t touch you at all, Dean. You don’t have to worry about this. I’m sorry I wasn’t more careful sooner.”

“What the fuck are you talking about, Cas? I never said that.”

“I—I apologize. I misunderstood.”

“Look, it’s nothing you did wrong, okay? But you signed up for sex with a man, not—_this_.”

Castiel squinted. “I want a relationship with you, Dean.”

Dean pulled a leg up to his chest. “Yeah, but— You went into this thinking you’d have sex with a man. Someone with a penis. You didn’t sign up for sex with _this_, so—”

“I did ‘sign up,’” and despite the fact that Cas rarely used awkward air quotes anymore, Dean could still hear them, “for sex with you. I’m only a man some of the time. My last vessel was a woman. I’m still myself.”

“Yeah, well. I don’t know.”

“You’re still a man, Dean. You’re just a man who has breasts and a vulva.”

Dean stared. “Yeah. That’s _weird_.”

“For you, perhaps. And I understand that, believe me, but you may want to try and look at the bright side here.” Castiel’s gaze turned sharp, dark—_piercing_. “You’re a man who has a clitoris.”

Of their own volition, Dean’s eyebrows climbed to his hairline. “Uh-huh. You can’t seriously find that hot, can you?”

“The idea of you having multiple orgasms? I’ve watched porn, Dean. I believe I could get you to come five times in ten minutes.”

Dean’s eyes bulged. “Are you fucking crazy? My dick would fall—_oh_.”

Cas nodded slowly. He looked like a goddamn predator stalking his prey. “If you’re uncomfortable, we don’t need to even speak of this again, but—”

“Could—could we? It sounds… good. Mostly.”

“What’s the mostly?” And Cas was completely in his sex headspace—which was basically super concerned for Dean’s well-being, as ridiculous as it got. Cas during sex was basically Mother Hen: Super Sexy Edition. 

“I don’t— What if I panic or something? I don’t know, maybe it’ll be too weird and I can’t calm down.”

“We don’t have to do this at all. And—”

“But I want to.”

“We can stop any time you want, for any reason. But I don’t think that was the answer you were looking for, was it, Dean?”

Dean shook his head slowly. “Not exactly.”

“And what was the answer you wanted?”

He licked his lips. “That… that you’d, um… do what we did a couple weeks ago.”

“When I gagged you on my cock?” Cas said it so fucking calmly, but his pupils were _shot_. 

Dean nodded. “Yeah. I didn’t—I didn’t have to think about anything except not choking.”

“It made you focused on the physical.”

This was what he loved about Castiel so much. That he could ask Cas to gag him with his cock and Cas would just _get it_. No judgment, just understanding. 

“I love you,” Dean said impulsively. Rare for him, actually, because he usually got too choked up, but. Whatever. 

Cas grinned, wide and brilliant. “I love you, too.” 

And that was another thing. Cas always said it. He didn’t even say, “I love you,” he always said, “I love you, _too_.”

Dean sat up and carefully pulled Cas into a kiss that felt too nervous and strange and weird but it felt like coming home but using a new key. It still fit, it just felt different in his hand. It was still home—it was still _Cas_—but he was the different one. 

Cas’ mouth was warm and soft and unhurried, and Dean finally started relaxing enough to not hunch into himself trying to his his breasts—to not _worry_ about it. 

For the first time in a week, the shape of his body didn’t matter so horribly much. 

And then Cas was slipping a hand up his shirt and Dean tensed for a second again and tried to remember that Cas didn’t care what Dean looked like. 

Dean still broke away from the kiss, though, needing a second to catch his breath. 

“You okay?” Cas asked softly, hands still resting on his bare skin, on his _hips_—which, seriously, he had _hips_ now—but not moving them. Just waiting to hear what Dean said. 

“I’m okay. Keep thinkin’ you’ll decide this is too much for you.”

Cas pulled away and Dean’s heart sank. 

_So it was too much. _

“I want to eat you out and gag you with my cock while I do that. What do you think about that?”

Dean stared. And then he nodded, rapidly, blood rushing down and he could feel himself getting slick and wet—and it was a weird sensation, but it wasn’t _bad_ weird. It was just… different. 

“Yeah,” he said, “yeah, I want that. Do you—”

“Lie back,” Cas said, and Dean did, accidentally kicking his headphones off the bed, completely uncaring of whether they broke into a hundred pieces or not. 

Cas moved up the bed, covering Dean’s body with his own, and—okay, so there was a good part of this that Dean hadn’t considered. 

A _really_ good part of this. 

Cas could _dwarf_ him. He could cover Dean, could make him feel small and protected and safe. Usually Dean was the taller, bigger one, but now it was Castiel. 

“Do you want your shirt to stay on?”

Dean hesitated. “For now?”

Cas nodded. “Of course. Is it okay if I take off your pants?”

“Yeah, go for it.”

Cas shifted and sat back on his heels and lifted Dean’s hips easily, muscles bulging so fucking _beautifully_, and then tugged his sweatpants off, smirking the way he only did right before he started fucking Dean into the _ground_. “I bet you taste so fucking good.”

Also, Dean really loved this about Cas, too—the guy was almost incompetent with social interactions _still_, but he knew how to dirty talk. 

Cas stripped out of his own clothes, throwing everything to the side, his boxer briefs thrown so hard they slapped against the wall but Dean couldn’t think about that for very long because Cas’ cock was three inches from his vagina and that—was a whole new level of weird, but it wasn’t bad weird. Not anymore. 

Before Dean could overthink it, though, Cas was turning, repositioning, and straddling Dean’s head and this—this was much more familiar ground, sucking Cas off. 

Cas’ warm breath ghosted over Dean’s cunt and Dean couldn’t keep focusing on having a cunt anymore and instead took Cas’ cock into his mouth, pressing Cas’ hips down with one hand and using his other to hold Cas’ balls. 

And then there was hot slick warmth on what had to be his clit and Dean groaned around Cas’ cock and Cas fucked down into Dean’s mouth and then everything got too overwhelming for him to focus on anything other than Cas’ cock, huge and hot and hard and _heavy_ on his tongue, working its way down his throat steadily until Cas was doing what Dean had begged for a couple weeks ago—making him focus on just not choking—and Cas’ tongue licking along him, and Cas’ groans and grunts and moans that seemed half from Dean sucking his cock and half from how Dean tasted, judging by the, “God, you suck cock so well, Dean, shit, you taste so fucking _good_.”

Cas suddenly stopped the long, wide licks and changed to _su_—

Dean’s hips jerked and he completely lost his train of thought, forgetting to suck Cas, trying to not come, even though that was irrational, it was fine, he was safe, this was _Cas_ who dragged him out of hell and risked not only his life but the lives of his entire garrison, he wouldn’t endanger Dean _now_, but it—

Dean came. 

Everything went warm and soft and sharp jolts of pleasure went thrumming through his body, every muscle tensing as it took everything in him not to scream with ecstasy. He held his breath and—and _shit_ did that backfire, because it just kept going until he let it out and sucked in another lungful of oxygen, pulling away from Cas to gasp, choked off breaths as his vagina clenched and squeezed and let go, the way that he’d thought women did on purpose but _obviously that was not the fucking case_ because Dean couldn’t have stopped it if he tried. 

“Oh, my god,” Dean mumbled when it was finally over. “How fucking—”

“Thirty-eight seconds.” Cas lapped at his clit again only for Dean to slap weakly at him. “Sorry. Do you want to take a moment?”

Dean nodded slowly. “Yeah. Yeah, just, uh. Just a minute. Come up here.”

Cas did, wrapping an arm around his waist. “What do you think?”

“This is insane.”

“Good or bad?”

“Good. Like, really good.” Dean sighed and smiled. “Thank you, Cas.”

“Do you want to end this sexual encounter?”

Dean snorted and shook his head. “I’m not withdrawing my consent. Are you?”

Cas’ grip on him tightened. “Not even a little.”

“Well. I don’t know about you, but, uh. Fingering? Is a thing?”

Cas kissed him hard. “I’d love to finger you, Dean. Do you want me to use my mouth, too?”

“Actually, um, can you kiss me while you do it? Please? And then, uh, penetration?”

“Absolutely,” Cas said, and rolled Dean back onto his back, reaching down to tease at his cunt. 

Dean kissed him again, weaving his fingers into Cas’ short, thick hair. 

Cas pressed a finger into him, slow and steady, and Dean moaned. “More, please, Daddy.”

“Of course, Dean,” Cas said, and added another. Dean kept begging for more and Cas kept giving him more until Cas finally said, “They’re all in. Do you want my fist?”

Dean hesitated. He did, but that seemed like a terrible idea. 

“We can go as slow as you want,” Cas said. 

Dean nodded. “Yeah. Yeah, okay, Daddy. Put your fist in me.” 

The next thing Dean knew, his cunt was burning and he was tearing up, but it still felt so _good_. 

“Are you okay, Dean?” And there was Mother Hen Cas, back at it again. 

Dean smiled despite himself. “I’m good, Daddy. I’m so good. Keep going.” And he was, actually, and once he felt Cas’ wrist at his rim, the muscles gripping it tight, he realized that _Castiel, angel of the Lord, had his entire fucking hand in Dean Winchester, the Righteous Man. _Or. Righteous Woman, as the case may be at the moment. 

“You look beautiful,” Cas said, voice filled with pure awe. “You look so beautiful, Dean.”

That was another thing Dean loved about Cas—that Cas was effusive with his praise, and he didn’t stick to gendered compliments. 

_Wait, _why_ exactly had Dean been so convinced that Cas wasn’t going to want him like this? _

“Can you move, Daddy?” Dean chewed his lip. “Slow.”

“Of course,” Cas said. “Do you want me to close my fist?”

“Um. Not yet. Soon.”

“Let me know when you’re ready.” And with that, Cas started to thrust his open fist inside of Dean, using his free hand to thumb at his clit, and somehow propped himself up enough that none of this was a problem. 

Dean blinked his eyes open, realizing that he’d closed them, and then realized that Cas had his wings out and was using them like bizarre supports. 

“God, I love your wings,” Dean said, and then gasped as Cas’ hand twitched and pressed harder against something. “What in the fuck is _that_?”

Cas blinked. “What?”

“You just—you just rubbed—” Dean broke off in a moan as Cas pressed against _something_ again, harder still, and then Dean’s hips were bucking, trying to work Cas deeper inside of him, and Dean finally gasped out, “Close it, close your fist, fuck—_Daddy, fuck_—”

It was huge inside of him. Dean had never been this full, and honestly, he doubted that he would’ve been brave enough to try it out anally, but he’d _never been this full_. 

Cas let Dean work himself on his fist and started rubbing his clit again, with a renewed vigor that had Dean coming in a matter of moments, his cunt trying to squeeze tight around Cas’ fist and _failing_ and it—

He came again. Somehow. He came again, right on the heels of the last orgasm—or maybe this was the same orgasm, and he just wasn’t paying attention, but it wasn’t like he could focus on anything other than—

Dean’s breath punched out of him as Cas shifted, his fist moving, too. “Do you want me to fuck you, Dean?”

“You are.” It came out breathy and high and Dean couldn’t careless. 

“Allow me to rephrase, then—do you want me to fuck you with my cock.”

Dean nodded before the words even caught up to his conscious mind. “Yes, yes, please, fuck me, Daddy.”

And then Cas pulled out his fist and slipped his cock inside of Dean’s loose cunt, and Dean was so fucking _loose_, the muscles not tightened back up nearly enough, and Cas started _thrusting_, and it sounded so wet and sloppy that Dean was shivering and shaking and on the absolute edge just _listening_ to how absolutely _obscene_ it was. 

“Can’t— I can’t last very long, Dean. I apologize,” Cas said, fucking harder and faster, and Dean moaned, loud and long and waved a hand as casually as he could, waving it off. 

“Don’t worry about it, Daddy. Love you, Daddy.”

“I love you, too, Dean—_Dean_—”

And then Cas came, shooting inside of him and then pulling out and finishing across his cunt and his clit and his lower tummy and the bottom of his shirt that he still hadn’t taken off, and Dean shivered at the warmth of it—at how _claimed_ he looked, with Cas’ load all over him, marking him as _Castiel’s_. 

Dean hooked a leg around Cas’ waist and watched as Cas sent his feathers back to another plane and practically collapsed on top of Dean. 

Dean slapped at him until he rolled over to the side. 

“Sorry,” Dean said. “Can’t really do that as easily anymore.”

“I don’t expect you to,” Cas said, looking dazed, but he pulled Dean close to his body, cuddling him tight against him. “Thank you, Dean.”

Dean smiled. “Thanks, Cas.”

They laid there for a few minutes and then Dean said, “Hey, so do you maybe—”

“So get this,” and the door had flown open and Sam, still looking at his laptop, barged in. “It’s a time-limited curse—holy fuck, what are you— Nope. Nope. Not touching that. Uh. It’s— I just wanted to let you know that it’s four more hours, roughly speaking, and then you’re home free, okay, Dean?”

“Yep,” Dean said, squirming a little under Castiel. He wasn’t sure whether he was excited for this to be over with or disappointed that orgasms like these weren’t going to last forever. 

“Okay. Later, jerk.”

“Bitch,” Dean said, completely on autopilot, every free part of his brain entirely devoted to what the next four hours were going to look like. 

Sam closed the door behind him and Dean turned to Cas, waiting to see if he’d speak first. But when he didn’t, completely letting Dean take the lead—another thing Dean loved about him—Dean finally said, “So. Four hours.”

“Yes.”

Dean shrugged, rolling his shoulders that didn’t feel as awkwardly narrow as they had a few hours earlier. “Just saying, but that’s, uh… a fair amount of time.”

Cas’ eyes darkened. “Are you making a suggestion?”

Dean licked his lower lip. “Maybe.”

**Author's Note:**

> If you enjoyed, please consider leaving kudos or a comment. 
> 
> Next three days of Kinktober will feature Sterek. 
> 
> _This work was inspired by @NihilistShiro's Kinktober prompt list, available here: https://twitter.com/NihilistShiro/status/1162794889970511872 _


End file.
